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On the difference in decomposition of taxifolin and luteolin vs. fisetin and quercetin in aqueous media

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Abstract

The decomposition of flavonols quercetin and fisetin, flavone luteolin and flavanone taxifolin was studied in slightly alkaline solution under ambient conditions. The study was based on spectrophotometry and high-pressure liquid chromatography. Products formed by atmospheric oxygen oxidation and hydrolysis were identified by HPLC–DAD and HPLC–ESI-MS/MS. Only small differences in the chemical structure of flavonoids resulted in extremely variable oxidation pathways and products. Oxidation of flavonols led to the formation of both a benzofuranone derivative and several open structures. On the contrary, the benzofuranone derivative was not found as a product of taxifolin and luteolin oxidative decomposition. These compounds were oxidized to their hydroxylated derivatives and typical open structures. Quercetin was not identified as a possible oxidation product of taxifolin.

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References

  1. Gupta VK, Jain R, Radhapyari K, Jadon N, Agarwal S (2011) Anal Biochem 408:179

    Article  CAS  Google Scholar 

  2. Bandzuchova L, Selesovska R, Navratil T, Chylkova J, Novotny L (2012) Electrochim Acta 75:316

    Article  CAS  Google Scholar 

  3. Selesovska R, Bandzuchova L, Navratil T, Chylkova J (2012) Electrochim Acta 60:375

    Article  CAS  Google Scholar 

  4. Trskova R, Rychlovsky P, Nemcova I, Jegorov A (1995) Talanta 42:837

    Article  CAS  Google Scholar 

  5. Markovic JMD, Amic D, Lucic B, Markovic ZS (2014) Monatsh Chem 145:557

    Article  Google Scholar 

  6. Lohmann W, Karst U (2008) Anal Bioanal Chem 391:79

    Article  CAS  Google Scholar 

  7. Selesovska R, Janikova-Bandzuchova L, Chylkova J (2015) Electroanalysis 27:42

    Article  CAS  Google Scholar 

  8. Biesaga M, Pyrzynska K (2009) Crit Rev Anal Chem 39:95

    Article  CAS  Google Scholar 

  9. Hollman PCH, Arts ICW (2000) J Sci Food Agric 80:1081

    Article  CAS  Google Scholar 

  10. Kang SY, Kang JY, Oh MJ (2012) J Microbiology 50:293

    Article  CAS  Google Scholar 

  11. Khan N, Afaq F, Syed DN, Mukhtar H (2008) Carcinogenesis 29:1049

    Article  CAS  Google Scholar 

  12. Amic A, Markovic Z, Markovic JMD, Stepanic V, Lucic B, Amic D (2014) Food Chem 152:578

    Article  CAS  Google Scholar 

  13. Di Carlo G, Mascolo N, Izzo AA, Capasso F (1999) Life Sci 65:337

    Article  Google Scholar 

  14. Rice-Evans CA, Miller NJ, Paganga G (1996) Free Radic Bio Med 20:933

    Article  CAS  Google Scholar 

  15. Wang YH, Wang WY, Chang CC, Liou KT, Sung YJ, Liao JF, Chen CF, Chang S, Hou YC, Chou YC, Shen YC (2006) J Biomed Sci 13:127

    Article  CAS  Google Scholar 

  16. Wang YH, Wang WY, Liao JF, Chen CF, Hou YC, Liou KT, Chou YC, Tien JH, Shen YC (2004) Biochem Pharmacol 67:2251

    Article  CAS  Google Scholar 

  17. Madsen HL, Andersen CM, Jorgensen LV, Skibsted LH (2000) Eur Food Res Technol 211:240

    Article  CAS  Google Scholar 

  18. Ueda H, Yamazaki C, Yamazaki M (2002) Biol Pharm Bull 25:1197

    Article  CAS  Google Scholar 

  19. Gabor M, Eperjess E (1966) Nature 212:1273

    Article  CAS  Google Scholar 

  20. Timbola AK, de Souza CD, Giacomelli C, Spinelli A (2006) J Brazil Chem Soc 17:139

    Article  CAS  Google Scholar 

  21. Sokolova R, Ramesova S, Degano I, Hromadova M, Gal M, Zabka J (2012) Chem Commun 48:3433

    Article  CAS  Google Scholar 

  22. Ramesova S, Sokolova R, Degano I (2015) Electrochim Acta 182:544

    Article  CAS  Google Scholar 

  23. Ramesova S, Degano I, Sokolova R (2014) Electrochim Acta 133:359

    Article  CAS  Google Scholar 

  24. Ramesova S, Sokolova R (2014) Chem Listy 108:507

    CAS  Google Scholar 

  25. Ramesova S, Sokolova R, Degano I, Hromadova M, Gal M, Kolivoska V, Colombini MP (2011) Collect Czech Chem C 76:1651

    Article  CAS  Google Scholar 

  26. Jorgensen LV, Cornett C, Justesen U, Skibsted LH, Dragsted LO (1998) Free Radic Res 29:339

    Article  CAS  Google Scholar 

  27. Krishnamachari V, Levine LH, Pare PW (2002) J Agric Food Chem 50:4357

    Article  CAS  Google Scholar 

  28. Kocabova J, Fiedler J, Degano I, Sokolova R (2016) Electrochim Acta 187:358

    Article  CAS  Google Scholar 

  29. Ramesova S, Sokolova R, Tarabek J, Degano I (2013) Electrochim Acta 110:646

    Article  CAS  Google Scholar 

  30. Sokolova R, Degano I, Ramesova S, Bulickova J, Hromadova M, Gal M, Fiedler J, Valasek M (2011) Electrochim Acta 56:7421

    Article  CAS  Google Scholar 

  31. Pyszkova M, Biler M, Biedermann D, Valentova K, Kuzma M, Vrba J, Ulrichova J, Sokolova R, Mojovic M, Popovic-Bijelic A, Kubala M, Trouillas P, Kren V, Vacek J (2016) Free Radic Biol Med 90:114

    Article  CAS  Google Scholar 

  32. Trouillas P, Marsal P, Siri D, Lazzaroni R, Duroux JL (2006) Food Chem 97:679

    Article  CAS  Google Scholar 

  33. Ramesova S, Sokolova R, Degano I, Bulickova J, Zabka J, Gal M (2012) Anal Bioanal Chem 402:975

    Article  CAS  Google Scholar 

  34. Osman A, Makris DP, Kefalas P (2008) Process Biochem 43:861

    Article  CAS  Google Scholar 

  35. Barkova K, Kinne M, Ullrich R, Hennig L, Fuchs A, Hofrichter M (2011) Tetrahedron 67:4874

    Article  CAS  Google Scholar 

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Acknowledgments

This work is supported by the Grant Agency of the Czech Republic (14-05180S).

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Authors and Affiliations

  1. J. Heyrovský Institute of Physical Chemistry of ASCR, v.v.i., Dolejškova 3, 18223, Prague, Czech Republic

    Romana Sokolová, Šárka Ramešová, Jana Kocábová & Viliam Kolivoška

  2. Department of Chemistry and Industrial Chemistry, University of Pisa, Via Moruzzi 13, 56124, Pisa, Italy

    Ilaria Degano

  3. Institute of Chemistry of Organometallic Compounds, CNR, Via G. Moruzzi, 1, 56124, Pisa, Italy

    Emanuela Pitzalis

Authors
  1. Romana Sokolová
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  2. Šárka Ramešová
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  3. Jana Kocábová
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  4. Viliam Kolivoška
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  5. Ilaria Degano
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  6. Emanuela Pitzalis
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Correspondence to Romana Sokolová.

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Sokolová, R., Ramešová, Š., Kocábová, J. et al. On the difference in decomposition of taxifolin and luteolin vs. fisetin and quercetin in aqueous media. Monatsh Chem 147, 1375–1383 (2016). https://doi.org/10.1007/s00706-016-1737-3

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  • DOI: https://doi.org/10.1007/s00706-016-1737-3

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